


You Are So Pretty

by businessboyjared



Category: Silicon Valley (TV)
Genre: Cunnilingus, F/M, Pegging, Plot What Plot/Porn Without Plot, i know what i'm about son
Language: English
Status: Completed
Published: 2018-05-17
Updated: 2018-05-17
Packaged: 2019-05-08 06:49:01
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,206
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/14688723
Author URL: https://archiveofourown.org/users/businessboyjared/pseuds/businessboyjared
Summary: I don't have a clever summary for this. They fuck, okay?





	You Are So Pretty

**Author's Note:**

  * For [alethiometry](https://archiveofourown.org/users/alethiometry/gifts).



> PLEASE JOIN ME IN THE HALLFOYLE PIT
> 
> (title is from the song You Are So Pretty by thumpasaurus. clever i know)

Monica apparently likes to celebrate things. The bottle of champagne was a bit much, though Gilfoyle could appreciate the gesture. He certainly wasn’t going to turn it down, by any means.  
  
Now, Monica’s way of “celebrating” her new position at Pied Piper is lounging on the couch while Gilfoyle and Dinesh play Fortnite and throw occasional expletives at each other. Gilfoyle suspects it’s more about celebrating her leave from the previous job rather than the acquisition of this one. Although, Pied Piper does come with the freedom to smoke when and wherever she wants, something she’s already taking advantage of. The ashtray next to her is close to overflowing.  
  
“ _Fucking Gilfoyle!”_ Dinesh slams his controller down at another loss. Gilfoyle takes a swig of his beer to hide a smirk. “I’m going to bed.”  
  
“All worn out from the spanking I just gave you? Go rub some aloe on it, princess.”   
  
Dinesh glares at him and for a moment Monica can see his face get all flushed. He says nothing, just turns on his heel and stomps away. Gilfoyle laughs to himself when he hears Dinesh’s bedroom door slam a moment later.  
  
Monica reaches to where he’s sat on the other end of the couch and swats at his arm.  
  
“The fuck was that for?”  
  
“You are such a child,” She shakes her head, tamping the last of her cigarette down into the ashtray. “Like really, only young children treat their crushes like shit.”  
  
Gilfoyle blinks slowly at her, his equivalent of an eye roll, and heads for the kitchen. Monica assumes the night is over and prepares for the lonely drive back to her place when he returns with four beers, offering her two of them.   
  
They drink in silence for a few minutes. Monica lights up another cigarette for lack of anything else to do. She takes a few puffs and sees Gilfoyle reach his hand out, like he’s asking. Monica passes it; watches him take a long drag, sees his face relax as he exhales for twice as long.   
  
“I don’t have a crush on Dinesh.” He hands the cigarette back to her.  
  
“You just wanna spank him. Okay.” She secures the cigarette tightly between her lips and reaches down for the two controllers, handing one to Gilfoyle. “Up for an ass kicking?” She winks at him, and Gilfoyle takes a long sip from his beer to hide the color he feels rise in his cheeks.  
  
Monica’s cool. Gilfoyle would never tell her this, of course, but she’s really fucking cool. And he doesn’t mean it like most guys in the valley do, where she’s cool just because she plays video games and drinks beer and is willing to talk to him _and_ is sexually available. (Gilfoyle’s not actually sure about that last part.) She’s just Monica, who doesn’t take shit from any of the incredibly full of shit people she has to deal with on a day-to-day basis—himself included.   
  
They fall into a trance, playing and shooting and shoving each other. Monica jams the buttons like it’ll help her, and Gilfoyle tries and fails to hide his smug grin at the end of every round. Monica huffs and stands up from the couch, stretching her arms and neck in the process.   
  
Gilfoyle finally notices she’s still in her work clothes when his eyes fall upon the hem of her black pencil skirt, sees the way it rides up her thighs just the slightest bit before she smooths it back down. He thinks about offering her a pair of sweatpants or a flannel—literally anything he owns is probably more comfortable than the business casual get up she’s still in.   
  
“I’m getting another beer,” Monica says, and steps over Gilfoyle’s outstretched legs.  
  
“Bring me two more.”  
  
Monica shoots him a look, the same one he got in her office the other day.   
  
“…Please?”  
  
She gives him a _fuck you_ smile and leaves.  
  
Gilfoyle reaches for his phone, mostly looking for something to do that _doesn’t_ involve thinking about that day in her office. Richard had seemed downright terrified of her, but Gilfoyle remembers feeling weirdly hypnotized.   
  
_Gilfoyle, can_ you _help with any of that?_  
  
He had barely been listening, but not for a lack of trying.  
  
_When’s my birthday?_

 

December 6. (It’s not weird that he knows that. He knows everyone’s birthday, gets the information one way or another. He saw it on her LinkedIn.)  
  
_Do I live in a house, or an apartment?  
  
_ That one he didn’t know, but maybe she would let him find out?  
  
Gilfoyle gasps and nearly jumps out of his skin when he feels something wet and cold against the side of his neck. Monica just laughs and tosses the beers into his lap, then flops herself back down on the couch. He tries not to notice that they’re sitting hip-to-hip now.   
  
“Okay, _Gilf_ ,” She says, sternly at first but then breaking out into a laugh. It’s obvious she’s in the sweet spot between sober and tipsy, and when Gilfoyle catches himself staring at her lips for a second too long, he figures he probably is too. “We’re both adults here. Let’s make this more interesting.”  
  
Gilfoyle waits for her to say more, but she doesn’t, just grabs the controller again and prepares for battle.   
  
“We could make this round a drinking game. Take a drink every time you smash every button possible and practically break my controller,” He says, laughing at her faux-offended look.   
  
“Okay, then take a drink every time _you_ …” Monica looks around the room for a second. “Every time you are an asshole.” She brings her beer to her lips and takes a big gulp, holding eye contact all while Gilfoyle stares and flips her the bird. Some of it dribbles down the front of her blouse and Gilfoyle has a hard time not following it with his eyes.  
  
He begrudgingly takes a sip of his own beer, though mostly just to make Monica laugh.  
  
“Take a drink when…” Gilfoyle starts, then stops. Monica’s looking at him, her body now twisted to the side so she can use the back of the couch as an arm rest. She looks sexy, and Gilfoyle figures it wouldn’t kill either of them to tell her.   
  
“Take a drink when you wanna make out.”  
  
He almost physically cringes at the words, at how fucking _lame_ he sounds. He suddenly can’t remember the last time he actually tried to make a move on somebody. But then Monica’s hands are on him, one against his jaw and the other at the back of his neck, grabbing his hair and holding him in place as she melds their lips together.   
  
It’s a lot softer, more finessed than Gilfoyle had expected given the circumstances, and it feels nice. Gilfoyle doesn’t get to do _nice_ very often, it’s not really a part of his whole thing. But he thinks it could be from now on, if it means melting into the back of the couch while Monica nips playfully at his bottom lip.   
  
If Gilfoyle was kissing anybody else, he wouldn’t hesitate to kiss back twice as hard in order to show his partner who’s in charge. But with Monica…  
  
With Monica, he’s more than happy to let her grip his hair tighter, to pull his head back at an almost uncomfortable angle while she crowds into him. Her hair falls down around both of their faces and tickles his cheeks, and when Gilfoyle breathes out the tiniest laugh she teases the tip of her tongue into his mouth. He’s so wrapped up in the kiss that it takes him awhile to realize he isn’t doing anything with his hands. He finds her hip and squeezes, feeling a thrill go through him when Monica’s breath hitches.   
  
But then she’s pulling away, and _fuck_. She’s not into this. She’s not into _him_. Fuck.  
Monica places a hand on Gilfoyle’s upper thigh. “Should we go to your room?”  
  
“Yes. Yeah.”  
  
They both drain the last of their beer, and Gilfoyle silently leads the way.  
  
As soon as his bedroom door is shut and locked, Monica pulls Gilfoyle into another searing kiss. He shivers as her cold hands move down from his face to his neck and finally rest at his shoulders. She pushes at Gilfoyle’s flannel until he takes the hint and shrugs out of it.   
  
“Take your shirt off, too.” Monica says, still so close that he can feel her lips moving against his.   
  
And shit, he won’t say no to that. He pulls his shirt off and tosses it into the corner, then sees Monica sit on the edge of his bed. She stares at his body for a moment, and when she and Gilfoyle lock eyes she lifts an eyebrow as if to suggest that she’s ready for a show. He feels just the slightest bit self-conscious, but figures it’s not productive to what they’re doing now. _What_ are _they doing now?_ Gilfoyle unzips his jeans and steps out of them, not really trying to be sexy but feeling his ears get hot when Monica’s eyes drift down lower.   
  
She untucks her blouse from her skirt and pulls it over her head, and even though he knows it’s useless at this point, Gilfoyle tries to subtly adjust himself in his underwear. His dick twitches at the sight of Monica in her bra and skirt.  
  
They’re both just kind of looking at each other, and Gilfoyle thinks maybe he should say something. He could tell Monica how fucking incredible she looks right now, how much he likes kissing her. How he really wants to crawl into her lap and let her have her way with him.

 

Instead he mumbles, “I’m not like. Buff, or anything.”  
  
Monica snorts out a laugh. “What?”  
  
“Nothing. Can we go back to what we were doing?” Gilfoyle leans down to kiss her, and thankfully she lets him. It’s a weird angle, so he tries to guide her onto her back so they can at least both be on the bed.   
  
“C’mere,” Monica pats her knees. “I want you in my lap.”  
  
Gilfoyle feels his face burning, but nods anyway. Monica scoots back a little more on the bed, and Gilfoyle straddles her lap gingerly.  
  
“You’re not gonna crush me, Gilfoyle.” She grabs his hips and tugs until he’s fully seated, their chests flush against each other. “I like your body,” She whispers into a soft kiss, and Gilfoyle feels one of her hands run down his chest while the other rests firmly on the small of his back. He can’t help the small whine that escapes him when Monica sucks at his collarbone.   
  
Gilfoyle hums. “I thought you were only into scrawny dudes.”  
  
She pulls back and looks right at him, smiling but with a hint of danger in her eyes.  
  
“And what gave you that idea?”  
  
“You _did_ try to hit on Richard. And I wouldn’t be surprised if there was something between you and Jared.”   
  
Monica smacks his arm playfully. “I can’t believe you! Those two are… outliers, it doesn’t—”  
  
Gilfoyle laughs and leans in to place kisses along her jaw and neck. “I’m not offended,” He says. “I’m glad that you like my beer belly enough to want to fuck me. And stop hitting me.”  
  
Monica laughs and lets him kiss her for a while before grabbing his hair and tugging him to her face. “Does that mean I’m doing the fucking?”  
  
Gilfoyle’s breath catches at the implication. He’s sure Monica felt his dick pulse between them, and the air feels a little heavy in his throat but in a good way. The best way. Monica’s eyes dart down to his lips and then back up.  
  
“I—” He starts. Licks his lips. “You should.” He takes another shaky breath, then adds, “Please.”   
  
Monica’s lips are on his in a second, hungry and possessive and hot as fuck. Gilfoyle whines into her mouth when he feels her hands slip down, down over the waistband of his boxers to knead and grip at his ass.  
  
“Take these off.” She says, leaning back on her hands to watch Gilfoyle scramble up and off her lap to step out of his boxers. He stands naked in front of her, feeling his whole body itch with need as she takes her time admiring the view.   
  
Monica reaches behind her to unhook her bra, then brings a hand up to pinch at her nipples. Gilfoyle sighs and takes his dick in hand.  
  
“I didn’t say you could touch yourself, Gilf.” Monica smirks as Gilfoyle drops his hand. He crawls onto the bed, kissing Monica until she’s flat on her back.   
  
“If I can’t touch myself can we at least get to the good part?” Gilfoyle huffs as he kisses down her neck. Monica laughs and rolls them over, pinning Gilfoyle with surprising strength. He groans when he feels her grind against him, the fabric of her skirt a little rough on his dick but still perfect. Monica kisses down his body slowly, taking pleasure in the way Gilfoyle whines with impatience at every kiss and bite she places along his chest.   
  
“Is this not the good part?” She whispers and then runs her tongue over one of his nipples.   
  
“ _Fuuuuck_ , it’s so good. Monica—” His voice breaks when he feels Monica’s teeth scrape against the other.   
  
Monica keeps her lips and hands busy as she follows the thin line of body hair down to Gilfoyle’s groin. She digs her nails into one hipbone and uses her other hand to spread his thigh wider. Gilfoyle stares at her, watches her kiss and lick and suck at every part of him except where he needs her mouth the most.   
  
“Please,” He groans, throwing his head back into the pillow.  
  
Monica lifts her head to look at him with feigned innocence. “Please what, Gilfoyle?”  
  
Gilfoyle grips helplessly at the hand on his hip. “I need you—your mouth, _fuck_!” His hips almost lift off the bed when he finally feels Monica suck the tip of his dick into her mouth, her tongue moving in painfully slow circles around it. She pulls off just a moment later, and Gilfoyle feels like he might cry.   
  
“Do you want my mouth, or my fingers?”  
  
He doesn’t even need to think twice. “Fingers. Please.”  
  
Monica grins and leans up to kiss him. “You’re really fucking cute when you beg. I’m assuming you have the right supplies?”  
  
Gilfoyle nods, and his whole body feels like jelly when he sits up to reach for the chest of sex toys he keeps beneath his bed. He tosses a bottle of lube, a blue dildo (one of his favorites), and a harness onto the bed. Monica takes the opportunity to slip out of her skirt and panties, then surveys the items with an impressed look while Gilfoyle gets back into position. She leans back over him to suck at his collarbone when he tugs at her hair.   
  
“This is officially me begging. _Please_ put your fingers in my ass or I might die. Please!”   
  
Monica sits up and grabs the bottle of lube, winking at Gilfoyle as she spreads some over her fingers. She kneels back down between his legs and much to Gilfoyle’s relief, he feels a hand wrap around his dick with just enough pressure for him to let out a pleasurable sigh. Her fingers trace and rub at his rim for what seems like forever. Gilfoyle whines petulantly and pushes his ass against her hand, trying to get her to take the hint, until finally, _finally thank god_ , he feels the tip of one finger slowly press inside him. Monica watches his face, looking for any sign of discomfort.  
  
“This okay?”   
  
“Yes, yes, keep going, fuuuck—” Monica cuts off his moans with a kiss, their tongues rolling lazily together as Gilfoyle pants into her mouth. She keeps fucking him with her index finger, slow and steady strokes until Gilfoyle starts pushing against her once more. She pulls away from his mouth and slows her hand, just leans over him and watches as he scrunches his eyes closed and bites his lip and tries to fuck himself on the one finger.   
  
“ _Fucking hell_ , you are so hot. Do you want another finger?”  
  
Gilfoyle nods, not even bothering to open his eyes, just grips weakly at any inch of her he can get his hands on. Monica slows her movements, and Gilfoyle is in pure agony until he feels a second finger push into him. He feels so good he barely remembers to breathe, only able to focus on Monica and her lips and her fingers and her touch that makes his muscles melt. He feels her smile against his lips, and then twist her fingers in a way that makes his jaw slacken and his toes curl. Gilfoyle clutches at her, panting and silently begging her to keep doing _that_. She hits his prostate a few more times, then backs off, thrusting and scissoring her fingers more gently before adding a third.   
  
“You like getting fucked?” Monica asks sweetly, her lips pressed right against the shell of his ear. Gilfoyle shivers, can’t help the gentle _yeah_ that escapes his mouth. “Mhm. Can’t wait to have my dick, can you?”   
  
Gilfoyle cries out at that, at how hot and perfect and _right_ she is. “Want it,” he moans loudly as she thrusts her hand harder and faster against him. “Want you to fuck me, Monica, now, _please_!” He feels his thighs tremble and there’s a split second when he’s worried he’ll come too soon—but Monica removes her fingers and squeezes him just tight enough to keep his orgasm at bay.  
  
He lays there, chest heaving while he tries to catch his breath, and watches Monica fiddle with the dildo and harness until it’s secured around her waist. She kneels at the end of the bed, both of them locking eyes for one heated moment before Monica settles in between his legs. She runs her hands along the inside of his thighs, appreciating the soft hair and thick muscles there, and Gilfoyle spreads them wider to make room. She looks fucking obscene, with her face flushed and long hair sticking to the sweaty parts of her skin while she spreads lube over the dildo jutting out from between her legs.  
  
“You are so pretty,” Gilfoyle blurts, and Monica grins down at him. She grabs the base of the dildo and presses the tip against his entrance, leaning down to prop herself up with one hand. Almost immediately, she feels Gilfoyle wraps his legs around her waist, in an attempt to get her deeper inside him.  
  
“Fuck, Gilfoyle, give me a second. I don’t wanna hurt you,” She huffs.  
  
“You won’t, just—” Gilfoyle’s voice dies in his throat as he feels her enter him. “Oh _fuck_ ,” He whimpers.  
  
Monica pauses when about half of the dildo is inside him, and almost laughs aloud at how quickly Gilfoyle protests this. He squeezes his thighs tighter and grips her arm.  
  
“ _Monicaaaaa!_ ” He realizes his whining sounds like that of a child but he needs to get fucked _now_ , or so help him Satan.  
  
She doesn’t say anything, just leans down with both hands to give herself some leverage and shallowly fuck into him. Gilfoyle’s mouth opens on a silent moan, and Monica takes the opportunity to suck and bite at his bottom lip. She keeps the same steady pace while pushing deeper inside him, and when she hits his prostate, Gilfoyle grunts helplessly into her mouth.  
  
“Harder,” He gasps, and Monica is about to ask _what’s the magic word?_ before he adds, “ _Please_ , Monica. Please fuck me harder, fuck—” She cuts him off with a rough thrust, slow ones at first before she gains speed, her own ragged breaths roaring loud in his ears.   
  
“Yeah, like that? You like taking my cock?” Gilfoyle just nods weakly, answering instead by thrusting his hips down to meet hers. Monica moans and lifts herself upright, one hand on Gilfoyle’s hip and the other reaching down to tug at his neglected dick. Her touch is fucking _perfect_ , twisting and squeezing her fist every so often while she jerks him in time with her thrusts. His back arches almost painfully, like his whole body is trying to get more of Monica all around and inside him.   
  
“ _Shit_ , Monica, I’m—”  
  
Monica speeds up her fist at that, still fucking into him but at a more manageable pace while Gilfoyle moans and writhes beneath her.  
  
“That’s right, baby,” She gasps and swipes a thumb over the head of his dick. “You gonna come on my dick?”  
  
“Oh _jesus christ_ , fuck—!” Gilfoyle’s voice catches in his throat as he comes hard over his stomach and Monica’s fist. He thinks he might have even blacked out for a second, because when he finally has the energy to open his eyes, Monica’s out of the harness and has a tissue in her hand to help clean him up.   
  
“You don’t have to do that,” He says, then reaches a limp arm out to take the tissue from her. Monica just smiles at him and kisses his belly when she’s done.   
  
“Was that good?” She asks, slightly out of breath herself as she lies down next to Gilfoyle.  
  
“ _So_ fucking good.” Gilfoyle laughs, then turns on his side to face Monica. He considers her for a second before saying, “I could eat you out, if you want,”  
  
Monica quirks an eyebrow at him, clearly up for the suggestion. He drapes himself over her, leaning down to kiss her a little roughly while he trails a hand down to one of her breasts. She moans into his mouth as he rubs his thumb over her nipple. Gilfoyle kisses her neck, her collarbone, leading down slowly to her chest.  
  
When Gilfoyle gets his mouth around her other nipple, she says, “Maybe if you ask nicely, I’ll let you.”  
  
Gilfoyle looks up at her from between her tits and she just smirks down at him. He scrapes his teeth against her nipple and says, “I see. Please, may I eat your pussy?” He makes his way down her stomach and pauses to lick at her belly button.  
  
Monica’s breath hitches. “You can do better than that, Gilf. I just heard how sweetly you can beg,” Gilfoyle grins up at her like, _you motherfucker_. She’s good. He keeps kissing down her body, pushes her legs apart and feels his mouth water at the sight of her. Part of him wants to say fuck it and just bury his face there until Monica’s had enough, but he knows the rules. Gilfoyle nips at the inside of her thigh.  
  
He can’t even tear his eyes away from her when he asks again. “Monica, please…”   
  
Just for fun, Monica reaches her hand down, runs her fingers between her folds and rubs at herself slowly while Gilfoyle watches. He swallows thickly, then tries again.   
  
“ _Fuck_ , Monica, _please_ let me eat you out. Please, fucking hell you look _delicious_ —”  
  
Monica moans at that and pulls her hand away. “Do it.”  
  
Gilfoyle doesn’t need to be told twice. He’s got his mouth on her in an instant, runs his tongue all around and over her just to get a taste. It takes a minute for Monica to get used to the sensation of his beard rubbing against her, but feels grateful at how soft it is. She places a hand on his head, gripping his hair roughly when she feels him suck and nip at her labia.   
  
“Oh fuck, you’re good at that,” She moans, grinding against him. Gilfoyle just runs his tongue along her, tracing shapes and letters and any other trick he can remember. He doesn’t touch her clit until she really starts panting above him, both hands in his hair now and gripping tightly. He brings his hand up around her hip, and Monica practically screams when she feels his fingers brush against her clit. Gilfoyle can’t help but smile into her, sucking even harder while he rubs her faster.   
  
She’s basically riding his face at this point, holding his head still and moving her hips against his mouth, _his perfect fucking mouth_ , while Gilfoyle works hard to keep the same rhythm in his hands and tongue.   
  
“Ahhh, yes—right there, f-fuck,” Monica gasps and comes on his face, Gilfoyle unable to tear his eyes away while her whole body shakes with pleasure above him. Gilfoyle moans while he licks gently at her, careful not to overstimulate. He slows his hand and finally stops his movements completely when he feels Monica lift his head up. She pulls him to her face to kiss him lazily, and they both groan when she tastes herself on his tongue. After a few minutes of breathless kisses, Gilfoyle flops onto his back, this time both of them taking a moment to steady their heaving chests.  
  
“Shit,” Monica says.   
  
Gilfoyle chuckles softly. “We are… really good at that.”  
  
“ _Fuck_ yeah, we are,” She lifts her arm up and they high-five weakly.  
  
Gilfoyle pulls her close, pressing her head against his chest before they promptly fall asleep.


End file.
